Holiday Homes in The Berkshires

"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "

"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"

"Stayed here multiple times and will come back again. Great place to stay…"

"Our family had a wonderful experience and stay. "

"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."

"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."

"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."

"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...

"Proximity to Catamount was ideal. Short drive to Great Barrington. The place was nice and sunny, and very comfortable. The mud room was fantastic for stowing gear and dressing in ski clothes. Overall, a very nice property. "

"Very quaint location, clean property, and great place to stay"

"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "

"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."